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Latrunculins: NMR study,two new toxins and a synthetic approach
Authors:Y Kashman  A Groweiss  R Lidor  D Blasberger  S Carmely
Institution:Department of Chemistry, Tel-Aviv University, Ramat-Aviv, 69 978 Tel-AvivIsrael
Abstract:A complete 1H and 13C NMR assignment of one of the latrunculins (B) was accomplished with the aid of 2D NMR COSY and CH shift-correlation experiments. The various H-H Coupling constants have been datermined and a conformation of the macrolide and the tetrahydropyran (THP) ring suggested on basis of the J-values and measured NOE's. The absolute configuration of latrunculin-A(1) was determined on the grounds of its earlier X-Ray analysis, and a chemical degradation to a known compound. Two novel latrunculins, -C(3) and -D(4), were isolated from the Red Sea sponge L. magnifica and their structures elucidated. Starting with L-cysteine a synthon for the latrunculins has been synthesized.
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